Identification of β-hydroxy fatty acid esters and primary, secondary-alkanediol esters in cuticular waxes of the moss Funaria hygrometrica

Lucas Busta, Jessica M. Budke, Reinhard Jetter

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The plant cuticle, a multi-layered membrane that covers plant aerial surfaces to prevent desiccation, consists of the structural polymer cutin and surface-sealing waxes. Cuticular waxes are complex mixtures of ubiquitous, typically monofunctional fatty acid derivatives and taxon-specific, frequently bifunctional specialty compounds. To further our understanding of the chemical diversity of specialty compounds, the waxes on the aerial structures of the leafy gametophyte, sporophyte capsule, and calyptra of the moss Funaria hygrometrica were surveyed. Respective moss surfaces were extracted, and resulting lipid mixtures were analyzed by gas chromatography-mass spectrometry (GC-MS). The extracts contained ubiquitous wax compound classes along with two prominent, unidentified classes of compounds that exhibited some characteristics of bifunctional structures. Microscale transformations led to derivatives with characteristic MS fragmentation patterns suggesting possible structures for these compounds. To confirm the tentative structure assignments, one compound in each of the suspected homologous series was synthesized. Based on GC-MS comparison with the authentic standards, the first series of compounds was identified as containing esters formed by β-hydroxy fatty acids and wax alcohols, with ester chain lengths varying from C42 to C50 and the most prominent homolog being C46. The second series consisted of fatty acid esters of 1,7-alkanediols, linked via the primary hydroxyl group, with ester chain lengths C40-C52 also dominated by the C46 homolog. The β-hydroxy acid esters were restricted to the sporophyte capsule, and the diol esters to the leafy gametophyte and calyptra. Based on their homolog and isomer distributions, and the presence of free 1,7-triacontanediol, possible biosynthetic reactions leading to these compounds are discussed.

Original languageEnglish (US)
Pages (from-to)38-49
Number of pages12
JournalPhytochemistry
Volume121
DOIs
StatePublished - Jan 1 2016
Externally publishedYes

Bibliographical note

Funding Information:
The assistance of S. Komar and E. Magat with extraction of F. hygrometrica leafy gametophytes is recognized with appreciation, as is the technical assistance and advice of C. Peng on the diol ester synthesis. This work has been made possible by generous support from the Natural Sciences and Engineering Research Council (Canada), the Canada Research Chairs Program , the Canada Foundation for Innovation , the US National Science Foundation ( DEB-1146295 ), and a Katherine Esau Postdoctoral Fellowship to J.M.B.

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

  • Bryophyta
  • Calyptra
  • Cuticular wax
  • Esters
  • Funaria hygrometrica
  • Gametophyte
  • Sporophyte
  • Structure elucidation
  • Very-long-chain

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